Find short term rentals in Chesapeake, VA at the best prices

561 available short term rental offers

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Chesapeake, VA short term rentals
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Best Short term and Weekly rentals in Chesapeake, VA

Best Chesapeake, VA luxury short term rentals

Southern Charm
Warm And Welcome - Chesapeake, VA
9.6 87 reviews
Chesapeake, VA
25/09 – 30/09
$240/nighttotal: $1200 (5 )

Southern Charm Warm And Welcome

2 4
apartment , Chesapeake
This Chesapeake apartment is located close to shopping and dining options, just a short distance from the interstate. It has received excellent ratings for its cleanliness, location, and overall user experience.
The apartment can comfortably accommodate up to four guests and features a fully equipped kitchen, a private garden with a fire pit and gas grill, and a washer and dryer for convenience. It also includes child-friendly amenities such as a highchair, pack and play, and a dedicated kiddie corner closet.

Best Chesapeake, VA Short term rentals with a jacuzzi

Among the 561 accommodations in Chesapeake, VA, here are the 4 best rentals with a jacuzzi

Condo ∙ 1 Bedroom ∙ 6 Guests - Chesapeake, VA
Chesapeake, VA
16/08 – 27/08
$292/nighttotal: $3212 (11 )

Condo ∙ 1 Bedroom ∙ 6 Guests

1 4
apartment , Chesapeake
This apartment is conveniently located near the Virginia Beach business district and General Dynamics in Chesapeake, a 40-kilometre drive from the Virginia Beach oceanfront. The surrounding area offers easy access to both business and leisure activities, making it a popular choice for travellers.
This one-bedroom apartment can accommodate up to six guests comfortably, with two queen beds and a sofa bed. Guests can enjoy a range of amenities, including a fully equipped kitchen, a swimming pool, a hot tub, a fitness centre, and free parking.
Serene Lodging With Indoor Fireplace - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
$140/nighttotal: $18060 (129 )

Serene Lodging With Indoor Fireplace

2 2
apartment , Virginia Beach
This Northwest Virginia Beach holiday home is situated 1.8km from Virginia Wesleyan University, within 5km of Sentara Leigh Hospital and Norfolk Premium Outlets.
This 71-square-metre property offers two bedrooms, one bathroom, sleeps two guests, and includes a fully equipped kitchen, Jacuzzi, free Wi-Fi, and in-unit laundry facilities.
The Chesapeake Gray\n\nhistorical Waterside District\n20 Mins To Oceanfront    \N\n - Chesapeake, VA
9.6 4 reviews
Chesapeake, VA
09/07 – 14/07
$663/nighttotal: $3315 (5 )

The Chesapeake Gray\n\nhistorical Waterside District\n20 Mins To Oceanfront \N\n

3 5
apartment , Norfolk
This Norfolk apartment is located within easy reach of both Waterside Festival Marketplace and Virginia Beach Town Center, offering a convenient base for exploring the city and its surroundings. The apartment is just a short drive from the beach, providing a perfect blend of urban convenience and coastal charm.
The property is a spacious three-bedroom home that comfortably sleeps six guests. It offers a modern kitchen, a private backyard with a patio, and a jacuzzi, ideal for relaxing after a day of exploring the local attractions.
Serene Retreat - Hot Tub, Private Dock & Fire Pit - Chesapeake, VA
Chesapeake, VA
31/07 – 31/08
$115/nighttotal: $3565 (31 )

Serene Retreat - Hot Tub, Private Dock & Fire Pit

1 2
apartment , Portsmouth
This private, fully furnished flat, with its own entrance, is located in a peaceful residential area of Portsmouth, offering waterfront views and direct access to a private dock.
This accommodation comfortably sleeps two, features a separate bedroom, a living room with a convertible sofa, a breakfast bar, air conditioning, a hot tub, and parking, making it ideal for a relaxing stay.

Frequently Asked Questions about short term rentals in Chesapeake, VA

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Best family friendly Chesapeake, VA Short term rentals

Among the 561 accommodations in Chesapeake, VA, here are the 4 best family friendly rentals

First Floor Guestroom - Chesapeake, VA
9.6 10 reviews
Chesapeake, VA
19/07 – 18/10
$71/nighttotal: $6461 (91 )

First Floor Guestroom

1 1
apartment , Chesapeake
This Chesapeake guesthouse offers a private, keyed-entry ground-floor room with a twin XL bed, ideal for solo travellers, and features a dedicated workspace with hardwired internet and Wi-Fi.
The single-occupancy room includes a mini-fridge, 32-inch smart TV with Netflix, and ample storage, boasting excellent cleanliness and guest ratings, plus on-site parking, a swimming pool and garden.
Olde Towne 4 Bedroom -2200 Sq Ft - Chesapeake, VA
9.4 313 reviews
Chesapeake, VA
23/06 – 25/06
$237/nighttotal: $474 (2 )

Olde Towne 4 Bedroom -2200 Sq Ft

1 3
apartment , Portsmouth
This Portsmouth apartment is located just a few hundred metres from the Strawbery Banke Museum and a 1 kilometre walk from Market Square, offering easy access to the city's historic district and attractions. The apartment has received excellent user ratings for its location, cleanliness, and overall experience.
This two-unit property provides ample space for larger groups or families, with each unit containing two bedrooms and a bathroom. Guests can enjoy a range of amenities, including fully equipped kitchens, in-unit laundry facilities, smart locks, WiFi, TVs, and comfortable bedding.
Cheerful 2 Bedroom Home Near Virginia Wesleyan - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
$256/nighttotal: $33024 (129 )

Cheerful 2 Bedroom Home Near Virginia Wesleyan

2 2
apartment , Virginia Beach
This private two-bedroom townhome is located on a corner cul-de-sac lot in the Northwest district of Virginia Beach, offering a quiet setting just a short drive to First Landing State Park and the Virginia Aquarium.
This 89 square meter residence accommodates up to four guests, featuring a fully equipped kitchen with a wine cooler, a screened-in porch, an extra-large sectional sofa, and high-speed WiFi, with contactless entry for a seamless self-check-in experience.
Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8 - Chesapeake, VA
9.2 7 reviews
Chesapeake, VA
24/07 – 26/07
$680/nighttotal: $1360 (2 )

Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8

4 4
apartment , Portsmouth
This holiday home is located in Portsmouth, just 1.5 km from Rivers Casino Portsmouth, and within 10 km of Portsmouth City Park and Frank D Lawrence Stadium. It has consistently received excellent user ratings, making it a popular choice for travellers.
The property offers 93 square metres of space and can comfortably accommodate up to 6 guests in its 3 bedrooms. The kitchen comes equipped with a fridge, microwave, oven, and dishwasher, while the garden provides a relaxing outdoor space. Guests can also enjoy free Wi-Fi, air conditioning, a terrace, and parking.

Best Chesapeake, VA lodging with parking

Sojourn At Colley Manor Unit 2 - Chesapeake, VA
10 2 reviews
Chesapeake, VA
12/10 – 18/02
$203/nighttotal: $26187 (129 )

Sojourn At Colley Manor Unit 2

2 2
apartment , Norfolk
This Ghent flat in Norfolk is centrally located near Colley Avenue's restaurants and shops, within easy reach (by foot, bike, bus, or Tide light rail) of Norfolk city centre and major hospitals such as CHKD and Norfolk General Hospital, and a short drive (approximately 20-30 km) from Virginia Beach and Ocean View Beach.
This 93-square-metre (1000 sq ft) two-bedroom, one-bathroom apartment sleeps four, offering self-check-in, a fully equipped kitchen (including fridge, microwave, and dishwasher), air conditioning, parking, and internet access; pack 'n' play and high chair rentals are available for families.
Steps To Elizabeth River & Dtwn! Portsmouth Condo - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
$131/nighttotal: $16899 (129 )

Steps To Elizabeth River & Dtwn! Portsmouth Condo

1 2
apartment , Portsmouth
This one-bedroom flat in Portsmouth is situated 8 minutes' walk from the Portsmouth Naval Shipyard Museum and 6 minutes' walk from the Commodore Theatre.
This 56 square metre apartment accommodates two guests and features a fully equipped kitchen, air conditioning, on-site parking, and internet access, with a coin-operated laundry facility conveniently located nearby.
Charming 1-bedroom In-law Suite With Functional Kitchen In Pleasant Portsmouth - Chesapeake, VA
9.6 4 reviews
Chesapeake, VA
14/08 – 16/08
$319/nighttotal: $638 (2 )

Charming 1-bedroom In-law Suite With Functional Kitchen In Pleasant Portsmouth

1 2
apartment , Portsmouth
This one-bedroom flat in Portsmouth is situated a 19-minute drive from Town Point Park and 40 minutes from Chesapeake Bay, offering convenient access to the Chrysler Museum of Art and the Children's Museum of Virginia.
This pet-friendly apartment accommodates up to three guests and includes on-site parking, complimentary Wi-Fi, air conditioning, and essential amenities such as towels, linens, and soap, with a check-out time of 12:00.
Historic Private Guest Apartment - Chesapeake, VA
10 5 reviews
Chesapeake, VA
25/09 – 30/09
$396/nighttotal: $1980 (5 )

Historic Private Guest Apartment

2 4
apartment , Norfolk
This private apartment, located in Norfolk's West Freemason district, offers easy walking access to the riverfront, local shops, and dining establishments, with the Children's Museum of Virginia and Lamberts Point Golf Course approximately 3 kilometres away.
This family-friendly flat accommodates up to four guests and features two bedrooms, one bathroom, air conditioning, a fully equipped kitchen with a fridge, microwave, and dishwasher, a separate living area, and an in-unit washer and dryer.
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